(Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester
• CAS No.: 80365-95-3
• Molecular Formula: C₃₁H₅₀O₇S
• Molecular Weight: 566.8
• Mol file: 80365-95-3.mol

Synonyms:

Chemical Property of (Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester

There total 23 articles about (Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

dimethyl 2-oxoheptylphosphonate (36969-89-8) → (Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester (80365-95-3,89616-91-1,89616-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) CrO₃, 2.) NaH / 1.) pyridine, 0 deg C, 20 min, 2.) THF, r.t., 2 h

2: 46 percent / NaBH₄ / methanol / 15 h / -40 °C

With chromium(VI) oxide; sodium tetrahydroborate; sodium hydride; In methanol;

DOI:10.1016/S0040-4020(01)88649-X

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester (80365-95-3,89616-91-1,89616-92-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) DIBAL, 2.) dimsylsodium / 1.) toluene, -78 deg C, 20 min, 2.) DMSO, 45 deg C, 2 h, 3.) ether

2: 88 percent / PCC / CH₂Cl₂ / 1.5 h

3: 1.) NaBH₄, 2.) Et₃N / 1.) MeOH, -40 deg C, 15 min, 2.) CH₂Cl₂, -25 deg C, 30 min

4: 400 mg / NaH / dimethylsulfoxide / 24 h / 45 °C

5: PPTS / methanol / 1 h / 60 °C

6: 43 percent / Et₃N / CH₂Cl₂ / 0.33 h / -25 °C

7: 1.) camphorsulfonic acid, 2.) KF / 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) HMPT, 60 deg C, 20 min

8: 1.) CrO₃, 2.) NaH / 1.) pyridine, 0 deg C, 20 min, 2.) THF, r.t., 2 h

9: 46 percent / NaBH₄ / methanol / 15 h / -40 °C

With chromium(VI) oxide; potassium fluoride; sodium tetrahydroborate; camphor-10-sulfonic acid; dimsylsodium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)88649-X

Reference yield:

methyl-6-formyl-3-cyclohexenecarboxylic acid (78647-11-7,80365-79-3,146388-94-5) → (Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester (80365-95-3,89616-91-1,89616-92-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 75 percent / NaBH₄ / methanol / 0.17 h / -40 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 0.25 h / -25 °C

3: 84 percent / 1 h / 60 °C / HMPT

4: 100 percent / 5percent KOH / ethanol / 0.5 h / Ambient temperature

5: 73 percent / KHCO₃, I₂, KI / H₂O / 6 h / Ambient temperature

6: 83 percent / DBU / benzene / 1.5 h / Ambient temperature

7: 100 percent / NaBH₄ / ethanol / 0.83 h / Ambient temperature

8: p-TsOH / CH₂Cl₂ / 0.33 h / 0 °C

9: 100 percent / 10percent NaOH / ethanol / 16 h / 100 °C

10: 1.) KI, I₂, KHCO₃, 2.) p-TsOH / 1.) water, 1 h, r.t., 2.) CH₂Cl₂

11: 92 percent / n-Bu₃SnH, ABIN / benzene / 0.5 h / 15 °C / Irradiation

12: 1.) DIBAL, 2.) dimsylsodium / 1.) toluene, -78 deg C, 20 min, 2.) DMSO, 45 deg C, 2 h, 3.) ether

13: 88 percent / PCC / CH₂Cl₂ / 1.5 h

14: 1.) NaBH₄, 2.) Et₃N / 1.) MeOH, -40 deg C, 15 min, 2.) CH₂Cl₂, -25 deg C, 30 min

15: 400 mg / NaH / dimethylsulfoxide / 24 h / 45 °C

16: PPTS / methanol / 1 h / 60 °C

17: 43 percent / Et₃N / CH₂Cl₂ / 0.33 h / -25 °C

18: 1.) camphorsulfonic acid, 2.) KF / 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) HMPT, 60 deg C, 20 min

19: 1.) CrO₃, 2.) NaH / 1.) pyridine, 0 deg C, 20 min, 2.) THF, r.t., 2 h

20: 46 percent / NaBH₄ / methanol / 15 h / -40 °C

With chromium(VI) oxide; potassium fluoride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; camphor-10-sulfonic acid; dimsylsodium; iodine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; potassium iodide; In methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4020(01)88649-X

upstream raw materials:

(Z)-7-[(1S,2R,4S,6S)-2-Acetylsulfanyl-6-((E)-(R)-3-hydroxy-oct-1-enyl)-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-hept-5-enoic acid methyl ester

acetyl chloride

dimethyl 2-oxoheptylphosphonate

(4-carboxybutyl)triphenylphosphonium bromide

Downstream raw materials:

(Z)-7-[(1S,2S,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

(Z)-7-[(1S,2S,4S,6R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-6-acetylsulfanyl-4-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

(9,11)-Epithio-(11,12)-methylene-TXA₂

(Z)-7-[(1S,2R,3R,5S)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-6-thia-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid